I’ll never forget my first time going out crossdressed, even though it’s almost eight years ago now. I had been dressing at home for many, many years and underdressing as often as I could, but I had never been out ‘en-femme’ before. A few weeks earlier I had joined a local crossdressing group and had finally plucked up the courage to attend a Tri-Ess meeting.
In my infinite wisdom I thought it would be a good idea to go out crossdressed for the first time. I was conservative in my femininity – I wore a blue blouse over some slightly feminine jeans with a bra for my breastforms and just a dash of makeup. With trepidation I exited my apartment, eager to quickly make the trip down two flights of stairs to my car without being seen. Then as I step foot into the parking lot I’m confronted by
Cops, everywhere – and they’re after crossdressers!
And I’m dressed. They’ll notice my boobs and my feminine blouse. Oh God! Now I’ve gone and done it I knew I shouldn’t have dared to venture out crossdressed. I almost died of embarrassment right there. I knew I was going to get into trouble, or at least a stern rebuke.
As it turns out, the police officer wasn’t outside my apartment waiting for crossdressers and he didn’t pay me much mind. I got into my car without any problems, and was off to my first Tri-Ess meeting.
Over exaggerated fear of what will likely never happen. That’s what I experienced the first time I went out crossdressed, and I have a hunch that I’m not alone. Our worst fears rarely come to pass yet we spend so long dwelling on them. It’s only when we’re out in the moment that the fear can be replaced with the joy of expressing one’s feminine self.
Going Out Crossdressed For the First Time
A few weeks ago I was blessed to take my good friend Vicki on her first crossdressing expedition into the cisgender world. She had visited the Emerald City (a local transgender club in Seattle) before, but leaving the safety of an understanding transgender group was new for her. We started out the afternoon with lunch at Chinese restaurant that we had all to ourselves, and despite some interesting smiles from our hosts it was a great way to ease into crossdressing in public.
Vicki truly showed mastery of her nerves when she suggested a quick trip to the mall together. Dining in a deserted restaurant is one thing, walking through a crowded mall is quite another. It was wonderful to see the sense of joy and accomplishment in her face as she took a proud step forward into the world as her feminine persona.
What was you first time going out crossdressed like? Was it nerve wracking, exciting, joyous, liberating or something else entirely? I’d love to hear, comment and let me know.
More Articles by Vanessa Law
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The first time I cross dressed outside was at high school on break up day. It was sort of a traditional thing that happened every year. I wore a friends catholic school girl uniform. So Awesome! Have a bunch of my own now!
Melody ♥
The first time I went out I went to the crosdresser friendly store where I bought all my stuff at the time. I was nervous. and when I asked if I was passing she said “No" I totally lost my confidence and changed my clothes in her dressing room. Gosh!!! I am going out today and it is the first time in 7 years and I am starting to get cold feet. Help me please.
I have been dressing for a long time, but I still find at times that are uncomfortable stares. I also found that one of the best places to ‘get out of the closet’ for the first time is a casino like in Alantic City they don’t pay much attention to you, they are more interested in their gambleing – but you get confidence
I have been out as myself 4 times now since I wrote the paragraph on October 9th. The first time I was awake for half the night thinking about it. And I got in my mind that I wanted to go to Dots where I bought my boots. I was wearing my new sweater dress. My new boots and various under clothes including breast forms and smoothing shape wear. Well I gave them a call from the parking lot and when I talked to Robin. She said sure You’re fine. I felt so good.Robin was her usual bubbly self and… Read more »
MY wife and i went out i was dressd enfemme we snuck out the door at nite to go for a ride to go see my brother he is gay and he knows my fetish but hasnt seem me yet dressed anyway my wife is drving my van and im in passdnges seat in a pretty 1 pc flower print dress when a deer runs out in frnt of us needless to say it died and we had to cal the police and im stil dressed SO EXCITING wow!
thats my type of luck, makes me nervous when i ride around dressed, but its the only way i can dress up. thats a funning story, good luck
Would love t o have a cd to chat with and try on clothes with
i understand what you are asking, i have been looking too, all the people i find want money for services and i not looking for that i love dressing and it would be nice to have a friend not a service
i was wondering i been going out dressed as a female the only problem i have my Boobs they stick out really good hard to miss when we are driving i am fine but when i get to the store or where ever i get scared some one will notices my breast my breast are real not forms can anybody help me to get over that anything you can tell me will help thank you
Alicia, if you are dressed as woman act like one and be proud of what you have naturally. I know quite a few others than would envy not having to wear forms or padded bras to accomplish the look of breasts. I understand what you are saying about the difference between driving and being out in the open. In the car you have that feeling of safety but when in a public place you become frightened. Don’t be! Be proud to let others see you as the woman you are. Straighten your posture, shoulders back and show them off like… Read more »
My first time out was to visit a professional photographer.
I posed very amateurishly but learned a lot about myself and my appearance.
The photographer was great and I was allowed to take my time and pose in various outfits.
It confirmed that I am passable even without any makeup.
I need to learn good makeup as that would really make the total package.
It was a very exciting experience, especially when guys peeked with obvious interest….
I would love to go to a CD friendly bar or nightclub.
Hi Vanessa! I just linked this article onto my website. I was so nervous the first time I actually got up the courage to walk out of my house! It wasn’t far, and I was dressed horribly. It was raining outside and I needed to bring in a trashcan. I was wearing a sports bra, pantyhose and a pair of green shorts. I went running out to get the bin, and realized I was actually outside! I stood still for a couple of seconds, enjoying the feeling of being out. Then I heard a sound from one of the neighbor’s… Read more »
I was recently trying out my very sexy new 4 inch heel thigh highs and managed to twinge something in my ankle or foot to cause major pain and swelling.
Of course I could not tell everyone how it happened……
I had always worn 3 inch heels so yesterday I purchased new four inch high heels to get accustomed.
Indeed they feel very nice and walked around in them for about a half hour with no ill effect.
You can face the fear of it and to just do it.Get it done.Its not really that bad of thing to do.It’s fun really.I get alot women complimenting me on the skirts i wear,or the boot and so on.I have always dressed on the feminine side.But for me,it feels like this is the way it should be.I do not feel that “weirdness" or “uncomfortable" feeling that im sure guys get when they go into the public view.I had one person ask me “where do you go dressed like that" ? I then said, “where do you go when you are… Read more »